Hydrochloric Acid → 1-Carboxymethyl-cyclopentanecarboxylic acid benzyl ester

HRID 2384080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2384080
[CH2:1]([O:8][C:9]([C:11]1([CH2:16][CH:17]=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:19].[Na+].Cl>C1COCC1.[Ag]=O>[CH2:1]([O:8][C:9]([C:11]1([CH2:16][C:17]([OH:19])=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86648214HCID 86648214, Verbindung

Produkt 1

HCID 216902921-Carboxymethyl-cyclopentanecarboxylic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 92152Silver(II) oxideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Next, to a solution of 1-(2-oxo-ethyl)-cyclopentanecarboxylic acid benzyl ester (200 mg, 0.81 mmol) in THF (5 mL) is added silver(II) oxide (201 mg, 1.62 mmol) and aqueous 1M NaOH (0.81 mL of 1.0 N, 0.81 mmol) and the suspension is stirred at room temperature for 18 hours. The mixture is acidified to pH 3 with aqueous 1M HCl and is extracted with ethyl acetate. The organic layer is washed with water, brine, dried over MgSO4 and filtered. The solvent is removed under reduced pressure to furnish 1-carboxymethyl-cyclopentanecarboxylic acid benzyl ester MS 263.3 (M+1).

Aufarbeitung

  1. extractionis extracted with ethyl acetate
  2. washThe organic layer is washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe solvent is removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9668cef015af4c149f98cd8a8ee927ea
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263629B2

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